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CHEBI:66334 - xanthohumol B

Default Structure
ChEBI IDCHEBI:66334
ChEBI Namexanthohumol B
Stars
DefinitionA member of the class of chalcones that is (2E)-1-(3,4-dihydro-2H-chromen-6-yl)-3-(4-hydroxyphenyl)prop-2-en-1-one substituted by hydroxy groups at position 3 and 5, a methoxy group at position 7 and geminal methyl groups at position 2. It has been isolated as a racemate from Humulus lupulus and has been shown to exhibit inhibitory activity against nitric oxide production.
Last Modified15 July 2013
DownloadsMolfile
FormulaC21H22O6
Net Charge0
Average Mass370.401
Monoisotopic Mass370.14164
SMILESCOc1cc2c(c(O)c1C(=O)/C=C/c1ccc(O)cc1)CC(O)C(C)(C)O2
InChIInChI=1S/C21H22O6/c1-21(2)18(24)10-14-16(27-21)11-17(26-3)19(20(14)25)15(23)9-6-12-4-7-13(22)8-5-12/h4-9,11,18,22,24-25H,10H2,1-3H3/b9-6+
InChIKeyGUQGMEWOCKDLDE-RMKNXTFCSA-N
Species of MetaboliteComponentSourceComments
Humulus lupulus (ncbitaxon:3486) - PubMed (15679315)
Roles Classification
Biological Roles:
EC 1.14.13.39 (nitric oxide synthase) inhibitor  An EC 1.14.13.* (oxidoreductase acting on paired donors, incorporating 1 atom of oxygen, with NADH or NADPH as one donor) inhibitor that interferes with the action of nitric oxide synthase (EC 1.14.13.39).
metabolite  Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
ChEBI Ontology
Outgoing Relation(s)
xanthohumol B (CHEBI:66334) has role EC 1.14.13.39 (nitric oxide synthase) inhibitor (CHEBI:61908)
xanthohumol B (CHEBI:66334) has role metabolite (CHEBI:25212)
xanthohumol B (CHEBI:66334) is a aromatic ether (CHEBI:35618)
xanthohumol B (CHEBI:66334) is a chalcones (CHEBI:23086)
xanthohumol B (CHEBI:66334) is a polyphenol (CHEBI:26195)
IUPAC Name 
(2E)-1-(3,5-dihydroxy-7-methoxy-2,2-dimethyl-3,4-dihydro-2H-chromen-6-yl)-3-(4-hydroxyphenyl)prop-2-en-1-one
Synonyms  Source
Dehydrocycloxanthohumol hydrateLIPID MAPS
rac-6-[3,4-dihydro-3,5-dihydroxy-7-methoxy-2,2-dimethyl-2H-benzo[b]pyrano]-3-(4-hydroxyphenyl)-2-propen-1-oneChEBI
rac-6'',6''-dimethyl-5''-hydroxy-4'',5''-dihydropyrano[2'',3'':4',3']-4,2'-dihydroxy-6'-methoxychalconeChEBI
rac-(E)-1-(3,5-dihydroxy-7-methoxy-2,2-dimethyl-3,4-dihydrochromen-6-yl)-3-(4-hydroxyphenyl)prop-2-en-1-oneChEBI
Manual XrefsDatabases
CPD-7127MetaCyc
EP2277526Patent
HMDB0034867HMDB
LMPK12120299LIPID MAPS
US2007218155Patent
WO2008095189Patent
Registry NumbersSources
Reaxys:7828262Reaxys
Citations